U.S. Pat. No. 3,536,733 teaches the preparation of compounds represented by the general formula ##STR2## where Y is F or CF.sub.3.
U.S. Pat. Nos. 3,214,478 and 3,242,218 teach a process for preparing compounds having the general formula ##STR3## where n is 0 or an integer greater than 0.
U.S. Pat. No. 3,250,806 teaches fluorocarbons having the general formula ##STR4## where
n=0 to 20;
R'.sub.f =perfluoroalkylene radical
COY is a carboxylic acid group or a carboxylic acid fluoride; and
X' is halogen or hydrogen.
German Pat. No. 1,238,458 teaches the reaction of iodo substituted perfluorocarboxylic acid fluorides with hexafluoropropylene oxide to make acid fluoride intermediates which can be pyrolyzed in the presence of an inorganic compound such as ZnO to produce vinyl ether compounds. The vinyl ether products, when copolymerized with tetrafluoroethylene form melt processable polymers that can be crosslinked by thermal decomposition of the perfluoro alkyl iodide. ##STR5## where n=1-8
p=0-5 PA1 m=0-5 PA1 n is at least 1. PA1 a=is 0 or an integer greater than 0; PA1 b=is 0 or an integer greater than 0; PA1 n=is 0 or an integer greater than 0; PA1 R'.sub.f and R.sub.f are independently selected from the group consisting of F, Cl, perfluoroalkyl and fluorochloroalkyl; PA1 X=F, Cl Br or mixtures thereof when n&gt;1; PA1 X'=Cl or Br; PA1 Y is a halogen such as Cl, Br, I or F; PA1 Z=F, Cl, Br, OH, NRR' or OA; PA1 R and R' are independently selected from the group consisting of hydrogen, or an alkyl having one or more than one carbon atom and aryl; and PA1 A=alkali metal, quaternary nitrogen, or R. PA1 b=is 0 or an integer greater than 0; PA1 n=0 or an integer greater than 0; PA1 m=0 or an integer greater than 0; PA1 R'.sub.f and R.sub.f are independently selected from the group consisting of F, Cl, perfluoroalkyl radicals and fluorochloroalkyl radicals; PA1 X=F, Cl or Br or mixtures thereof when n&gt;0; PA1 X' is independently Cl or Br. PA1 Y=I, F, Cl, or Br. PA1 b=is 0 or an integer greater than 0; PA1 n=0 or an integer greater than 0; PA1 R'.sub.f and R.sub.f are independently selected from the group consisting of F, Cl, perfluoroalkyl and fluorochloroalkyl; PA1 X=F, Cl or Br or mixtures thereof when n&gt;1; PA1 X'=Cl or Br or mixtures thereof; PA1 Y is a halogen such as Cl, Br, I or F; PA1 Z=F, Cl, Br, OH, NRR' or OA; PA1 R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atom and aryl; and PA1 A=alkali metal, quaternary nitrogen, or R. PA1 b=0 or integer greater than 0; PA1 n=0 or an integer greater than 0; PA1 R'.sub.f and R.sub.f are independently selected from the group consisting of F, Cl, perfluoroalkyl and fluorochloroalkyl; PA1 X=F, Cl, Br or mixtures thereof when n&gt;1; PA1 X'=Cl or Br; PA1 Y=I, Br, Cl or F PA1 b=is 0 or an integer greater than 0; PA1 n=is 0 or an integer greater than 0; PA1 R.sub.f ' and R.sub.f are independently selected from the group consisting of F, Cl, perfluoroalkyl and fluorochloroalkyl; PA1 X=F, Cl, Br or mixtures thereof when n&lt;1; PA1 X'=Cl or Br; PA1 Y is I, Br, Cl or F; PA1 Z'=OH, NRR' or OR; PA1 R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atom and aryl; and PA1 P is a cation or capable of forming a cation, such as Na.sup.+, K.sup.+, H.sup.+, etc.
A specific example being ##STR6##
U.S. Pat. No. 3,450,684 teaches the preparation of vinyl ethers by reacting an acid fluoride with hexafluoropropylene oxide followed by decarboxylation using an activator such as ZnO or silica according to the following reactions: ##STR7## where X is F, Cl, H, CH.sub.3, CF.sub.2 Cl or CF.sub.3
Copolymerization of these monomers with tetrafluoroethylene forms polymers having lower melt viscosity than the parent tetrafluoroethylene polymer.
U.S. Pat. No. 3,114,778 teaches the formation of vinyl ethers by reacting an acid fluoride with hexafluoropropylene oxide to produce an intermediate compound which may be decarboxylated to a vinyl ether according to the following reactions: ##STR8## where R.sub.f is, for example, a perfluoroalkyl radical. Homopolymers and copolymers, with tetrafluoroethylene, of the vinyl ethers is taught.
Fearn, et al, Journal of Polymer Science: Part A-1, Vol. 4, 131-140(1966) discloses that in the pyrolysis of sodium salts of carboxylic acids which contain fluorine and chlorine in the beta position, sodium chloride is preferentially, but not exclusively eliminated. For example: ##STR9##
U.S. Pat. No. 3,282,875 shows decarboxylation of intermediates to form various vinyl ethers. At higher temperatures of around 300.degree. C., vinyl ether yields of about 80% were obtained. When, however, lower temperatures of about 200.degree. C. were used to decarboxylate, yields of about 20-30% were obtained.
R. D. Chambers, in his book, Fluorine in Organic Chemistry, published by John Wiley & Sons, 1973, pages 211-212, teaches that carboxylic acid derivatives may be converted to olefins. The conversion involves the loss of carbon dioxide and forms an intermediate carbanion. The intermediate then looses NaF to form the resulting olefin.
Evans et al., in the Journal of Organic Chemistry Volume 33, page 1838, (1968) describes catalysts useful for the reaction between acid fluorides and epoxides.
M. Hudlicky in Chemistry of Organic Fluorine Compounds--2nd Edition, John Wiley & Sons, New York, pages 20-21, teaches the well-known reaction between tetrafluoroethylene and perfluoroalkyl iodides to form telomeric perfluoroalkyl iodides according to the following reaction: ##STR10##
Various methods for polymerization are taught in the following references: Emulsion Polymerization--Theory and Practice by D. C. Blackley, John Wiley & Sons; U.S. Pat. Nos. 3,041,317; 2,393,967; 2,559,752; and 2,593,583.